Test the Waters: Why Your Side Hustle is Your Safety Net

This week, I've been having conversations with several educators who are wrestling with the same question that kept me up nights a few years ago: Should I leave my school position to start my own business?

After talking with these folks, I want to share something that turned out to be crucial in my transition—something I stumbled into rather than strategically planned, but that I now consider essential advice for anyone contemplating this leap.

Start your side hustle now. While you're still employed.

I know, I know. You're already stretched thin. You're grading papers until midnight and answering parent emails during your "lunch" break. The last thing you need is another commitment. But hear me out.

The Difference Between Interest and Investment

Here's what I learned the hard way: there's a massive gap between people saying "That's a great idea—you should totally do that!" and those same people actually writing you a check. In my conversations with potential clients while I was still employed, I heard plenty of encouragement. Former colleagues would nod enthusiastically and say things like, "Schools definitely need that kind of help."

But getting a school to actually pay for something? That's an entirely different challenge altogether.

Schools are notoriously difficult clients when it comes to opening their wallets. Budgets are tight, decision-making processes are complex, and the buying cycle is tied to an academic calendar that doesn't care about your business timeline. Testing whether schools will actually invest in your services—not just express polite interest—is information you absolutely need before you give up that steady paycheck.

The Beauty of Nights and Weekends

Yes, running a side hustle while employed creates complications. You'll need to manage relationships and potential conflicts of interest carefully. You'll be tired. You'll have to turn down some opportunities because of timing constraints.

But you'll also get to test three critical things:

Do you actually like this work? Fantasizing about consulting is very different from actually doing it. A side hustle lets you discover whether you enjoy client management, proposal writing, and all the business development tasks that come with entrepreneurship.

Is there real market demand? You'll learn quickly whether schools are willing to pay for what you're offering, or if your great idea only sounds good in theory.

Can you handle the business side? Invoicing, contracts, scheduling, marketing—all of this becomes real when you're doing it, even part-time.

Perfect Timing for Testing

As we head into a new school year, this is actually ideal timing to explore a side hustle. Schools are settling into routines, identifying pain points, and are often more open to considering outside support as they realize what they need help with.

You can start small—maybe one project, one consultation, one workshop. See how it feels. See if you can get that first payment processed. Learn whether you're solving a problem schools actually want to pay to solve.

The Honest Truth

I can't say my side hustle was planned strategically—it just sort of happened. But looking back, it was the smartest thing I did. It gave me confidence, market validation, and a small but real revenue stream before I made the full transition.

If you're nervous about going out on your own (and you should be—it's a big decision), use that nervousness productively. Start testing your business idea now, while you still have the security of employment.

Your side hustle isn't just practice—it's your proof of concept.